Appendix 2-5: Rejected ecotox bibliography for Chlorpyrifos



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sarin, soman, and diazoxon) and less active toward others (such as paraoxon or chlorpyrifos ) relative to the variant *192R allele. Another allele that affects activity is *55M; PON1 enzyme quantity, rather than specific activity or substrate preference, is altered. The *192R variant occurs commonly with a frequency of 25-64% across the populations analyzed. The *55M allele is less common, occurring in 5-40% of individuals depending upon the ethnic group studied. These activity and allele frequency data were incorporated into Monte Carlo simulations in which the frequency of both variant alleles was simultaneously modeled in Caucasian, African American, and Japanese populations. The resulting Monte Carlo activity distributions were bimodal for the substrate paraoxon with approximately fourfold differences between low- and high-activity modal medians. Differences in activity between total population median and 1st percentile were five- to sixfold. When sarin metabolic variability was simulated, the population distributions were unimodal. However, there was an even greater degree of interindividual variability (median to 1st percentile difference >20-fold). These results show that the combined effects of two PON1 allelic variants yielded a population distribution that is associated with a considerable degree of interindividual variability in enzyme activity. This indicates that assessments involving PON1 substrates need to evaluate polymorphism-related variability in enzyme activity to display the distribution of internal doses and adverse responses. This may best be achieved via physiologically based pharmacokinetic (PBPK) models that input PON1 activity distributions, such as those generated in this analysis, to simulate the range of oxon internal doses possible across the population. [PUBLICATION ABSTRACT]
Keywords: Pharmacy And Pharmacology
Copyright - Copyright Taylor & Francis Ltd. 2009
Language of summary - English
Pages - 473-507
ProQuest ID - 760949745
Last updated - 2012-02-08
Place of publication - Philadelphia
Corporate institution author - Ginsberg, Gary; Neafsey, Patricia; Hattis, Dale; Guyton, Kathryn Z; Sonawane, Babasaheb; Johns, Douglas O
DOI - 2174669011; 55155651; 105332; JTXB; ContentEditor.105332.5606697 English

483. Giordano, Ady; Richter, Pablo; Ahumada, Ines, and Giordano, Ady. Determination of Pesticides in River Water Using Rotating Disk Sorptive Extraction and Gas Chromatography-Mass Spectrometry. 2011 Oct 15; 85, (5): 2425-2429.


Rec #: 47049
Keywords: FATE
Notes: Chemical of Concern: CPY
Abstract: Abstract: The rotating disk sorptive extraction (RDSE) technique was applied to the determination of pesticides in aqueous samples. Pesticides of different polarities were considered in this study: chlorpyrifos, diazinon, fenvalarate, cyhalothrin, cypermethrin, lindane and malathion. The sorptive/desorptive behavior of the pesticides was studied using a rotating disk containing a polydimethylsiloxane (PDMS) phase on one of its surfaces. The analyte polarity was a significant factor in the extraction time; shorter extraction times were required for the more apolar pesticides. The optimum variables for the extraction of all analytes were: extraction time of 3 h, sample volume of 25 mL, rotational velocity of the disk 1250 rpm, desorption time of 30 min using methanol. For pesticides with values of Log K sub(ow) 4, the extraction time can be reduced to 30 min for a quantitative extraction. Under these conditions, recoveries between 76% and 101% were obtained for the target pesticides, and the repeatability of the methodology, expressed as relative standard deviation, was determined to be between 10% and 20%. Additionally, the limits of detection of the analytes were lower than 3.1 mu g L super(-1). The extraction method developed using the RDSE was compared to a stir bar sorptive extraction (SBSE) under the same conditions. It can be observed that the extraction using the rotating disk offers higher recoveries because of its higher PDMS volume and its higher surface area to volume ratio that allows for improved mass transfer.
Keywords: AQ 00001:Water Resources and Supplies
Keywords: SW 3050:Ultimate disposal of wastes
Keywords: Agricultural Chemicals
Keywords: Desorption
Keywords: Standard Deviation
Keywords: Pesticides
Keywords: Mass Transfer
Keywords: Water Resources Abstracts; Aqualine Abstracts; ASFA 2: Ocean Technology Policy & Non-Living Resources
Keywords: Velocity
Keywords: Polarity
Keywords: Lindane
Keywords: Malathion
Date revised - 2012-05-01
Language of summary - English
Pages - 2425-2429
ProQuest ID - 926336592
SubjectsTermNotLitGenreText - Desorption; Agricultural Chemicals; Standard Deviation; Pesticides; Mass Transfer; Velocity; Lindane; Polarity; Malathion
Last updated - 2012-12-14
British nursing index edition - Talanta [Talanta]. Vol. 85, no. 5, pp. 2425-2429. 15 Oct 2011.
Corporate institution author - Giordano, Ady; Richter, Pablo; Ahumada, Ines
DOI - 2a0d9f39-2182-487e-bf69csaobj201; 15796163; 0039-9140 English

484. Glotfelty, D. E.; Seiber, J. N., and Liljedahl, L. A. Pesticides in Fog. 1987; 325, 602-605.


Rec #: 850
Keywords: FATE
Call Number: NO FATE (ACR,ATZ,CPY,DZ,MDT,MLN,MP,MTL,PDM,SZ,TBF)
Notes: Chemical of Concern: ACR,ATZ,CPY,DZ,EPRN,MDT,MLN,MP,MTL,PDM,PRN,SZ,TBF

485. Goda, S. K. ; Elsayed, I. E.; Khodair, T. A.; El-Sayed, W. , and Mohamed, M. E. Screening for and isolation and identification of malathion-degrading bacteria: cloning and sequencing a gene that potentially encodes the malathion-degrading enzyme, carboxylestrase in soil bacteria. 2010; 21, (6): 903-913.


Rec #: 60679
Keywords: FATE
Notes: Chemical of Concern: CPY
Abstract: Abstract: Five malathion-degrading bacterial strains were enriched and isolated from soil samples collected from different agricultural sites in Cairo, Egypt. Malathion was used as a sole source of carbon (50 mg/l) to enumerate malathion degraders, which were designated as IS1, IS2, IS3, IS4, and IS5. They were identified, based on their morphological and biochemical characteristics, as Pseudomonas sp., Pseudomonas putida, Micrococcus lylae, Pseudomonas aureofaciens, and Acetobacter liquefaciens, respectively. IS1 and IS2, which showed the highest degrading activity, were selected for further identification by partial sequence analysis of their 16S rRNA genes. The 16S rRNA gene of IS1 shared 99% similarity with that of Alphaprotoebacterium BAL284, while IS2 scored 100% similarity with that of Pseudomonas putida 32zhy. Malathion residues almost completely disappeared within 6 days of incubation in IS2 liquid cultures. LC/ESI-MS analysis confirmed the degradation of malathion to malathion monocarboxylic and dicarboxylic acids, which formed as a result of carboxylesterase activity. A carboxylesterase gene (CE) was amplified from the IS2 genome by using specifically designed PCR primers. The sequence analysis showed a significant similarity to a known CE gene in different Pseudomonas sp. We report here the isolation of a new malathion-degrading bacteria from soils in Egypt that may be very well adapted to the climatic and environmental conditions of the country. We also report the partial cloning of a new CE gene. Due to their high biodegradation activity, the bacteria isolated from this work merit further study as potential biological agents for the remediation of soil, water, or crops contaminated with the pesticide malathion.
Keywords: Malathion, Pesticide degradation, Pseudomonas, GC-ECD, Carboxylesterase
ISI Document Delivery No.: 666WL

486. Goel, P. and Kapur-Ghai, J. Development of an enzyme-linked immunosorbent assay for detection of the organophosphate pesticide, chlorpyrifos. 2012; 103, (9): 989-990.


Rec #: 60709
Keywords: CHEM METHODS
Notes: Chemical of Concern: CPY
Abstract: Keywords: TANDEM MASS-SPECTROMETRY, IMMUNOASSAY, FENTHION, SAMPLES, ELISA
ISI Document Delivery No.: 048AJ

487. Goldoni, M. ; Caglieri, A.; Poli, D.; Vettori, M. V.; Ceccatelli, S., and Mutti, A. Methylmercury at low doses modulates the toxicity of PCB153 on PC12 neuronal cell line in asynchronous combination experiments. 2008; 46, (2): 808-811.


Rec #: 60729
Keywords: IN VITRO
Notes: Chemical of Concern: CPY
Abstract: Abstract: Me-Hg and PCB153 are known neurotoxic contaminants which tend to accumulate in food, particularly in fish. Aim of this study was to perform asynchronous and combined exposure to Me-Hg and PCB153 in a neuronal rat cell line (PC12) to better characterise the antagonism observed at some combination concentrations. PC12 cells were treated with three concentrations of Me-Hg (0.1-0.5-1.0 mu M) and PCB153 at one concentration (175 mu M) in single and combined asynchronous exposures, using viability (MTT assay) as end-point. At all concentrations used, a statistically significant antagonistic effect was observed when Me-Hg preceded PCB 153 exposure, while effect was additive when PCB153 preceded Me-Hg exposure. The antagonism is particularly evident at low concentrations of Me-Hg (0. 1 mu M). In conclusion, combined asynchronous exposure showed that whereas Me-Hg can modulate PCB 153 toxicity, the opposite seems not to be true. Therefore, the use of asynchronous exposure could be a promising approach to study the mechanisms of toxicity of binary mixtures. (C) 2007 Elsevier Ltd. All rights reserved.
Keywords: methyl-mercury, PCB153, PC12, neurotoxicity, combined exposure
ISI Document Delivery No.: 268JZ

488. Goldsmith, M. and Tawfik, D. S. Potential Role of Phenotypic Mutations in the Evolution of Protein Expression and Stability.


Rec #: 50869
Keywords: NO TOXICANT
Notes: Chemical of Concern: CPY
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ABSTRACT: Phenotypic mutations (errors occurring during protein synthesis) are orders of magnitude more frequent than genetic mutations. Consequently, the sequences of individual protein molecules transcribed and translated from the same gene can differ. To test the effects of such mutations, we established a bacterial system in which an antibiotic resistance gene (TEM-1 beta-lactamase) was transcribed by either a high-fidelity RNA polymerase or its error-prone mutant. This setup enabled the analysis of individual mRNA transcripts that were synthesized under normal or error-prone conditions. We found that an increase of approximately 20-fold in the frequency of transcription errors promoted the evolution of higher TEM-1 expression levels and of more stable enzyme variants. The stabilized variants exhibited a distinct advantage under error-prone transcription, although under normal transcription they conferred resistance similar to wild-type TEM-1. They did so, primarily, by increasing TEM-1's tolerance to destabilizing deleterious mutations that arise from transcriptional errors. The stabilized TEM-1 variants also showed increased tolerance to genetic mutations. Thus, although phenotypic mutations are not individually subjected to inheritance and natural selection, as are genetic mutations, they collectively exert a direct and immediate effect on protein fitness. They may therefore play a role in shaping protein traits such as expression levels, stability, and tolerance to genetic mutations.
MESH HEADINGS: Ampicillin/pharmacology
MESH HEADINGS: DNA, Complementary/genetics
MESH HEADINGS: Databases, Nucleic Acid
MESH HEADINGS: *Evolution, Molecular
MESH HEADINGS: Gene Expression Regulation
MESH HEADINGS: Mutation/genetics
MESH HEADINGS: Phenotype
MESH HEADINGS: Selection, Genetic
MESH HEADINGS: Transcription, Genetic/drug effects/genetics
MESH HEADINGS: beta-Lactamases/*genetics/*metabolism eng

489. Gomes, J. and Lloyd, O. L. Oral exposure of mice to formulations of organophosphorous pesticides: gestational and litter outcomes. 2009; 19, (2): 125-137.


Rec #: 60749
Keywords: MIXTURE
Notes: Chemical of Concern: CPY
Abstract: Abstract: The purpose of this study was to examine gestational and litter outcomes in mice models from oral exposure to a mixture of formulations of organophosphorous pesticides used in local vegetable production. Male and female mice were exposed to premating and preconception, respectively, to a mixture of organophosphorous pesticide formulations for a period of 7 weeks. The pregnant dams were monitored during gestation and delivered by Caesarean section pre-partum. The percentages of resorptions and the resorptions/implantations ratios, in all the exposed groups, were significantly higher than the reference and the control groups. Percentages of litters with one or more lost embryos were observed in all the exposed groups and were significantly higher than the comparison groups. Fetal weights were significantly lower and the maternal weight gains per live fetus were significantly higher in the medium-dose-exposed groups than the control group. Percentages of fetuses with intra-uterine growth retardation at one standard deviation were significantly higher in all the exposed groups than the comparison groups.
Keywords: reproductive toxicity, organophosphorous pesticide formulations, fetal
ISI Document Delivery No.: 434SZ

490. Gomes, J.; Lloyd, O. L., and Hong, Z. Oral Exposure of Male and Female Mice to Formulations of Organophosphorous Pesticides: Congenital Malformations. 2008; 27, (3): 231-240.


Rec #: 2470
Keywords: MIXTURE
Call Number: NO MIXTURE (CPY,DDVP,PIRM)
Notes: Chemical of Concern: CPY,DDVP,PIRM

491. Gonz+ílez-Curbelo, Miguel +üngel; Hern+índez-Borges, Javier; Ravelo-P+_rez, Lidia M., and Rodr+ˇguez-Delgado, Miguel +üngel. Insecticides extraction from banana leaves using a modified QuEChERS method. 2011 Apr 1-; 125, (3): 1083-1090.


Rec #: 5420
Keywords: FOOD
Notes: Chemical of Concern: CPY
Abstract: An analytical method employing gas chromatography (GC) with nitrogenÇôphosphorus detection has been developed for the simultaneous determination of eight insecticides (seven organophosphorus pesticides: ethoprophos, diazinon, chlorpyrifos-methyl, fenitrothion, malathion, chlorpyrifos and fenamiphos, and one thiadiazine: buprofezin) in banana leaves that are currently being used to feed cattle or hogs. The extraction and preconcentration of these pesticides were carried out using a modified QuEChERS procedure and the whole method was validated in terms of repeatability, linearity, precision and accuracy. Triphenylphosphate was used as internal standard. Matrix effect evaluation was also carried out using a matrix matched calibration. The developed procedure gave satisfactory recovery (89Çô104%) and relative standard deviation values (<9.1%) for the studied pesticides in banana leaves, while limits of detection ranged between 0.002 and 0.064 mg/kg. The method was finally applied to the determination of these pesticides in 12 treated banana leaves samples collected at different banana cultivars of the Canary Islands. Residues of chlorpyrifos were found in ten of these samples. Pesticide confirmation was carried out by GC with tandem mass spectrometry detection. QuEChERS/ Insecticides/ Banana leaves/ Gas chromatography/ NitrogenÇôphosphorus detection/ Tandem mass spectrometry

492. Gonzalez-Curbelo, Ma; Hernandez-Borges, J; Borges-Miquel, T M; Rodriguez-Delgado, Ma, and Gonzalez-Curbelo, MA. Determination of Pesticides and Their Metabolites in Processed Cereal Samples. 2012 Jan; 29, (1): 104-116.


Rec #: 42929
Keywords: FOOD
Notes: Chemical of Concern: CPY
Abstract: Abstract: Fifteen pesticides including some of their metabolites (disulfoton sulfoxide, ethoprophos, cadusafos, dimethoate, terbufos, disulfoton, chlorpyrifos-methyl, malaoxon, fenitrothion, pirimiphos-methyl, malathion, chlorpyrifos, terbufos sulfone, disulfoton sulfone and fensulfothion) were analysed in milled toasted wheat and maize as well as in wheat flour and baby cereals. The QuEChERS (quick, easy, cheap, effective, rugged and safe) methodology was used and its dispersive solid-phase extraction procedure was optimised by means of an experimental design with the aim of reducing the amount of co-extracted lipids and obtaining a clean extract. Gas chromatography with nitrogen phosphorus detection were used as the separation and detection techniques, respectively. The method was validated in terms of selectivity, recoveries, calibration, precision and accuracy as well as matrix effects. Limits of detection were between 0.07 and 34.8 mu g kg-1 with recoveries in the range of 71-110% (relative standard deviations were below 9%). A total of 40 samples of different origin were analysed. Residues of pirimiphos-methyl were found in six of the samples at concentrations in the range 0.08-0.47 mg kg-1, which were below the MRLs established for this pesticide in cereal grains. Tandem mass spectrometry confirmation was also carried out in order to identify unequivocally the presence of this pesticide.
Keywords: Risk Abstracts
Keywords: Residues
Keywords: Lipids
Keywords: Metabolites
Keywords: Chlorpyrifos
Keywords: Triticum aestivum
Keywords: Food additives
Keywords: Zea mays
Keywords: Pesticides
Keywords: Economics
Keywords: R2 23060:Medical and environmental health
Keywords: Wheat
Keywords: Nitrogen
Date revised - 2012-09-01
Language of summary - English
Pages - 104-116
ProQuest ID - 1038614554
SubjectsTermNotLitGenreText - Chlorpyrifos; Food additives; Residues; Lipids; Economics; Pesticides; Metabolites; Wheat; Nitrogen; Triticum aestivum; Zea mays
Last updated - 2013-02-08
British nursing index edition - Food Additives & Contaminants: Part A - Chemistry, Analysis, Control, Exposure & Risk Assessment. Vol. 29, no. 1, pp. 104-116. Jan 2012.
Corporate institution author - Gonzalez-Curbelo, MA; Hernandez-Borges, J; Borges-Miquel, T M; Rodriguez-Delgado, MA
DOI - d9d1046b-f6e1-4501-ae26mfgefd107; 17032559; 1944-0049; 1944-0057 English

493. Gonzalez-Curbelo, Miguel Angel; Asensio-Ramos, Maria; Herrera-Herrera, Antonio V; Hernandez-Borges, Javier, and Gonzalez-Curbelo, Miguel Angel. Pesticide Residue Analysis in Cereal-Based Baby Foods Using Multi-Walled Carbon Nanotubes Dispersive Solid-Phase Extraction. 2012 Jul; 404, (1): 183-196.


Rec #: 42659
Keywords: CHEM METHODS
Notes: Chemical of Concern: CPY
Abstract: Abstract: In the present study, a new analytical method has been developed for the simultaneous quantification of 15 organophosphorus pesticides, including some of their metabolites, (disulfoton-sulfoxide, ethoprophos, cadusafos, dimethoate, terbufos, disulfoton, chlorpyrifos-methyl, malaoxon, fenitrothion, pirimiphos-methyl, malathion, chlorpyrifos, terbufos-sulfone, disulfoton-sulfone and fensulfothion) in three different types of commercial cereal-based baby foods. Dispersive solid-phase extraction (dSPE) with multi-walled carbon nanotubes (MWCNTs) was used together with gas chromatography with nitrogen phosphorus detection. Most favorable conditions involved a previous ultrasound-assisted extraction of the sample with acetonitrile containing formic acid. After evaporation of the extract and redissolution in water, a dSPE procedure was carried out with MWCNTs. The whole method was validated in terms of repeatability, linearity, precision and accuracy and matrix effect was also evaluated. Absolute recoveries were in the range 64--105 % with relative standard deviation values below 7.6 %. Limits of quantification achieved ranged from 0.31 to 5.50 Delta *mg/kg, which were lower than the European Union maximum residue limits for pesticide residues in cereal-based baby foods.
Keywords: Chlorpyrifos
Keywords: European Union
Keywords: P 9999:GENERAL POLLUTION
Keywords: Evaporation
Keywords: Pesticide residues
Keywords: Pesticides
Keywords: Metabolites
Keywords: Dimethoate
Keywords: Pollution Abstracts
Keywords: Malathion
Keywords: Nitrogen
Keywords: Nanotechnology
Date revised - 2012-11-01
Language of summary - English
Location - European Union
Pages - 183-196
ProQuest ID - 1171876842
SubjectsTermNotLitGenreText - Chlorpyrifos; Evaporation; Pesticide residues; Pesticides; Metabolites; Dimethoate; Malathion; Nitrogen; Nanotechnology; European Union
Last updated - 2013-02-08
British nursing index edition - Analytical and Bioanalytical Chemistry [Anal. Bioanal. Chem.]. Vol. 404, no. 1, pp. 183-196. Jul 2012.
Corporate institution author - Gonzalez-Curbelo, Miguel Angel; Asensio-Ramos, Maria; Herrera-Herrera, Antonio V; Hernandez-Borges, Javier
DOI - 957ed207-82f6-453a-b95acsamfg201; 17286135; 1618-2642 English

494. Goodbred, S. L.; Gilliom, R. J.; Gross, T. S.; Denslow, N. P.; Bryant, W. L., and Schoeb, T. R. Reconnaissance of 17beta-Estradiol, 11-Ketotestosterone, Vitellogenin, and Gonad Histopathology in Common Carp of United States Streams: Potential for Contaminant-Induced Endocrine Disruption. 1996: 60 p.


Rec #: 860
Keywords: NO DURATION,SEDIMENT CONC,SURVEY
Call Number: NO DURATION (ACR,ADC,ATZ,AZ,CBF,CBL,CPMR,CPY,DCPA,DEAL,DMT,DS,DZ,EP,EPTC,MCB,MLN,MP,MTL,OYZ,PDM,PPG,PPN,PPX,PRO,PRT,SZ,TBC,TBO,TFN), NO SEDIMENT CONC (ACR,ADC,ATZ,AZ,CBF,CBL,CPMR,CPY,DCPA,DEAL,DMT,DS,DZ,EP,EPTC,MCB,MLN,MP,MTL,OYZ,PDM,PPG,PPN,PPX,PRO,PRT,SZ,TBC,TBO,TFN), NO SURVEY (ACR,ADC,ATZ,AZ,CBF,CBL,CPMR,CPY,DCPA,DEAL,DMT,DS,DZ,EP,EPTC,MCB,MLN,MP,MTL,OYZ,PDM,PPG,PPN,PPX,PRO,PRT,SZ,TBC,TBO,TFN)
Notes: Chemical of Concern: ACR,ADC,AND,ATZ,AZ,BFL,CBF,CBL,CPMR,CPY,CZE,DCPA,DDT,DEAL,DLD,DMT,DS,DZ,EFL,EN,EP,EPRN,EPTC,HCCH,HPT,MBZ,MCB,MLN,MP,MRX,MTL,MXC,NPP,OYZ,PCH,PDM,PEB,PPCP,PPG,PPN,PPX,PRN,PRO,PRT,SZ,TBC,TBO,TFN,TRB,TRL,TXP

495. Graham, J. M. GLUT1 deficiency syndrome as a cause of encephalopathy that includes cognitive disability, treatment-resistant infantile epilepsy and a complex movement disorder. 2012; 55, (5): 332-334.


Rec #: 60829
Keywords: HUMAN HEALTH
Notes: Chemical of Concern: CPY
Abstract: Abstract: Glucose transporter-1 (GLUT1) deficiency syndrome is caused by heterozygous mutations in the SLC2A1 gene, resulting in impaired glucose transport into the brain. It is characterized by a low glucose concentration in the cerebrospinal fluid (hypoglycorrhachia) in the absence of hypoglycemia, in combination with low to normal lactate in the cerebrospinal fluid (CSF). It often results in treatment-resistant infantile epilepsy with progressive developmental disabilities and a complex movement disorder. Recognizing GLUT1 deficiency syndrome is important, since initiation of a ketogenic diet can reduce the frequency of seizures and the severity of the movement disorder. There can be a considerable delay in diagnosing GLUT1 deficiency syndrome, and this point is illustrated by the natural history of this disorder in a 21-year-old woman with severe, progressive neurological disabilities. Her encephalopathy consisted of treatment-resistant seizures, a complex movement disorder, progressive intellectual disability, and deceleration of her head growth after late infancy. Focused evaluation at age 21 revealed GLUT1 deficiency caused by a novel heterozygous missence mutation in exon 7 (c. 938C > A; p. Ser313Try) in SLC2A1 as the cause for her disabilities. (c) 2011 Elsevier Masson SAS. All rights reserved.
Keywords: Genetic encephalopathy, GLUT1 deficiency syndrome, SLC2A1, Absence
ISI Document Delivery No.: 989DJ

496. Gray, K. and Lawler, C. P. Strength in Numbers: Three Separate Studies Link in Utero Organophosphate Pesticide Exposure and Cognitive Development. 2011; 119, (8): A328-A329.


Rec #: 60839
Keywords: HUMAN HEALTH
Notes: Chemical of Concern: CPY
Abstract: Keywords: PRENATAL EXPOSURE, CHLORPYRIFOS, CHILDREN
ISI Document Delivery No.: 801MU

497. Greenstein, M. Phytoextraction of Chlorpyrifos Contaminated Soil Using Indian Mustard (Brassica juncea). SOIL; 1999; 165.


Rec #: 870
Keywords: NOT PURSUING,ABSTRACT
Call Number: NO ABSTRACT (CPY)
Notes: Chemical of Concern: CPY

498. Grigoryan, H.; Li, B.; Anderson, E. K.; Xue, W. H.; Nachon, F.; Lockridge, O., and Schopfer, L. M. Covalent binding of the organophosphorus agent FP-biotin to tyrosine in eight proteins that have no active site serine. 2009; 180, (3): 492-498.


Rec #: 60859
Keywords: HUMAN HEALTH
Notes: Chemical of Concern: CPY
Abstract: Abstract: Organophosphorus (OP) esters are known to bind covalently to the active site serine of enzymes in the serine hydrolase family. It was a surprise to find that proteins with no active site serine are also covalently modified by OP. The binding site in albumin, transferrin, and tubulin was identified as tyrosine. The goal of the present work was to determine whether binding to tyrosine is a general phenomenon. Fourteen proteins were treated with a biotin-tagged organophosphorus agent called FP-biotin. The proteins were digested with trypsin and the labeled peptides enriched by binding to monomeric avidin. Peptides were purified by HPLC and fragmented by collision induced dissociation in a tandem ion trap mass spectrometer. Eight proteins were labeled and six were not. Tyrosine was labeled in human alpha-2-glycoprotein 1 zinc-binding protein (Tyr 138, Tyr 174 and Tyr 181), human kinesin 3C motor domain (Tyr 145), human keratin I (Tyr 230), bovine actin (Tyr 55 and Tyr 200), murine ATP synthase beta (Tyr 431), murine adenine nucleotide translocase 1 (Tyr 81), bovine chymotrypsinogen (Tyr 201) and porcine pepsin (Tyr 310). Only 1-3 tyrosines per protein were modified, suggesting that the reactive tyrosine was activated by nearby residues that facilitated ionization of the hydroxyl group of tyrosine. These results suggest that OP binding to tyrosine is a general phenomenon. It is concluded that organophosphorus-reactive proteins include not only enzymes in the serine hydrolase family, but also proteins that have no active site serine. The recognition of a new OP-binding motif to tyrosine suggests new directions to search for mechanisms of long-term effects of OP exposure. Another application is in the search for biomarkers of organophosphorus agent exposure. Previous searches have been limited to serine hydrolases. Now proteins such as albumin and keratin can be considered. (C) 2009 Elsevier Ireland Ltd. All rights reserved.
Keywords: FP-biotin, Organophosphorus agent, Tyrosine, Non-cholinesterase, Mass
ISI Document Delivery No.: 471SA

499. Grigoryan, Hasmik; Li, Bin; Xue, Weihua; Grigoryan, Marine; Schopfer, Lawrence M., and Lockridge, Oksana. Mass spectral characterization of organophosphate-labeled lysine in peptides. 2009 Nov 1-; 394, (1): 92-100.


Rec #: 3060
Keywords: IN VITRO
Notes: Chemical of Concern: CPY
Abstract: Organophosphate (OP) esters bind covalently to the active site serine of enzymes in the serine hydrolase family. Recently, mass spectrometry identified covalent binding of OPs to tyrosine in a wide variety of proteins when purified proteins were incubated with OPs. In the current work, manual inspection of tandem mass spectrometry (MS/MS) data led to the realization that lysines also make a covalent bond with OPs.
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